Article ID Journal Published Year Pages File Type
5222271 Tetrahedron 2011 7 Pages PDF
Abstract

We have discovered a photocatalytic intramolecular hetero-Diels–Alder reaction of tethered bis(enones). This transformation involves the intermediacy of an enone radical anion and constitutes the formal coupling of an electron-deficient heterodiene with an electronically mismatched enone dienophile. The diastereoselectivity and regioselectivity of the process are high, and the dihydropyran products are amenable to a variety of synthetically useful transformations.

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Related Topics
Physical Sciences and Engineering Chemistry Organic Chemistry